Copper-mediated nucleophilic radiobromination of aryl boron precursors: Convenient preparation of a radiobrominated PARP-1 inhibitor
[Display omitted] •Copper-mediated nucleophilic radiobromination of aryl boron precursors.•Broad scope of aryl boron precursors.•Efficient and robust radiolabeling reactions.•High yield and feasible purification.•Used for the facile synthesis of a radiobrominated PARP-1 inhibitor. The copper-mediate...
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| Veröffentlicht in: | Tetrahedron letters 2018-05, Vol.59 (20), p.1963-1967 |
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| container_end_page | 1967 |
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| container_issue | 20 |
| container_start_page | 1963 |
| container_title | Tetrahedron letters |
| container_volume | 59 |
| creator | Zhou, Dong Chu, Wenhua Voller, Thomas Katzenellenbogen, John A. |
| description | [Display omitted]
•Copper-mediated nucleophilic radiobromination of aryl boron precursors.•Broad scope of aryl boron precursors.•Efficient and robust radiolabeling reactions.•High yield and feasible purification.•Used for the facile synthesis of a radiobrominated PARP-1 inhibitor.
The copper-mediated nucleophilic radiobromination of aryl boron precursors with a radiobromide ion is a novel radiolabeling method that is efficient and robust. High radiochemical conversion (RCC) was observed using a variety of solvents, temperatures and catalysts. The reaction is also clean and is feasible for purification to obtain high chemical and radiochemical purity. This method provides a very useful route for the preparation of radiobrominated pharmaceuticals, including a radiobromine labeled PARP-1 inhibitor, and it is a valuable addition to the family of copper-mediated radiolabeling processes. |
| doi_str_mv | 10.1016/j.tetlet.2018.04.024 |
| format | Article |
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•Copper-mediated nucleophilic radiobromination of aryl boron precursors.•Broad scope of aryl boron precursors.•Efficient and robust radiolabeling reactions.•High yield and feasible purification.•Used for the facile synthesis of a radiobrominated PARP-1 inhibitor.
The copper-mediated nucleophilic radiobromination of aryl boron precursors with a radiobromide ion is a novel radiolabeling method that is efficient and robust. High radiochemical conversion (RCC) was observed using a variety of solvents, temperatures and catalysts. The reaction is also clean and is feasible for purification to obtain high chemical and radiochemical purity. This method provides a very useful route for the preparation of radiobrominated pharmaceuticals, including a radiobromine labeled PARP-1 inhibitor, and it is a valuable addition to the family of copper-mediated radiolabeling processes.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2018.04.024</identifier><identifier>PMID: 30349147</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Auger electron radiation ; Boron reagents ; Bromine-76 ; Bromine-77 ; Labeling method ; Nucleophilic radiobromination ; PET imaging</subject><ispartof>Tetrahedron letters, 2018-05, Vol.59 (20), p.1963-1967</ispartof><rights>2018 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c529t-175e0db6d7714e6595f31d9bf0fe5fc3e993c17eb0ef4087ab851dbf458abc063</citedby><cites>FETCH-LOGICAL-c529t-175e0db6d7714e6595f31d9bf0fe5fc3e993c17eb0ef4087ab851dbf458abc063</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2018.04.024$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30349147$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhou, Dong</creatorcontrib><creatorcontrib>Chu, Wenhua</creatorcontrib><creatorcontrib>Voller, Thomas</creatorcontrib><creatorcontrib>Katzenellenbogen, John A.</creatorcontrib><title>Copper-mediated nucleophilic radiobromination of aryl boron precursors: Convenient preparation of a radiobrominated PARP-1 inhibitor</title><title>Tetrahedron letters</title><addtitle>Tetrahedron Lett</addtitle><description>[Display omitted]
•Copper-mediated nucleophilic radiobromination of aryl boron precursors.•Broad scope of aryl boron precursors.•Efficient and robust radiolabeling reactions.•High yield and feasible purification.•Used for the facile synthesis of a radiobrominated PARP-1 inhibitor.
The copper-mediated nucleophilic radiobromination of aryl boron precursors with a radiobromide ion is a novel radiolabeling method that is efficient and robust. High radiochemical conversion (RCC) was observed using a variety of solvents, temperatures and catalysts. The reaction is also clean and is feasible for purification to obtain high chemical and radiochemical purity. This method provides a very useful route for the preparation of radiobrominated pharmaceuticals, including a radiobromine labeled PARP-1 inhibitor, and it is a valuable addition to the family of copper-mediated radiolabeling processes.</description><subject>Auger electron radiation</subject><subject>Boron reagents</subject><subject>Bromine-76</subject><subject>Bromine-77</subject><subject>Labeling method</subject><subject>Nucleophilic radiobromination</subject><subject>PET imaging</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp9kctu1DAUhi0EosPAGyCUJZuE49jOhQVSNWpppUpUCNaW7ZwwHmXsYDsjsefB8WhKL5t6Y_n4_Ofyf4S8p1BRoM2nXZUwTZiqGmhXAa-g5i_IinYtK5no6EuyAuBQcmD9GXkT4w7yaTp4Tc4YMN5T3q7I342fZwzlHgerEg6FW8yEft7ayZoiqMF6HfzeOpWsd4UfCxX-TIX2Ib_mgGYJ0Yf4udh4d0Bn0aVjeFbhQfC0TO5xe_79tqSFdVurbfLhLXk1qiniu7t7TX5eXvzYXJU3375eb85vSiPqPpW0FQiDboa2pRwb0YuR0aHXI4woRsOw75mhLWrAkUPXKt0JOuiRi05pAw1bky-nuvOi88ImDxvUJOdg93kr6ZWVT3-c3cpf_iAb2guWTVuTj3cFgv-9YExyb6PBaVIO_RJlTeumB6gbllP5KdUEH2PA8b4NBXkEKHfyBFAeAUrgMgPMsg-PR7wX_Sf2sANmow4Wg4wmu24yv0wjycHb5zv8A8Ots10</recordid><startdate>20180516</startdate><enddate>20180516</enddate><creator>Zhou, Dong</creator><creator>Chu, Wenhua</creator><creator>Voller, Thomas</creator><creator>Katzenellenbogen, John A.</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20180516</creationdate><title>Copper-mediated nucleophilic radiobromination of aryl boron precursors: Convenient preparation of a radiobrominated PARP-1 inhibitor</title><author>Zhou, Dong ; Chu, Wenhua ; Voller, Thomas ; Katzenellenbogen, John A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c529t-175e0db6d7714e6595f31d9bf0fe5fc3e993c17eb0ef4087ab851dbf458abc063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Auger electron radiation</topic><topic>Boron reagents</topic><topic>Bromine-76</topic><topic>Bromine-77</topic><topic>Labeling method</topic><topic>Nucleophilic radiobromination</topic><topic>PET imaging</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhou, Dong</creatorcontrib><creatorcontrib>Chu, Wenhua</creatorcontrib><creatorcontrib>Voller, Thomas</creatorcontrib><creatorcontrib>Katzenellenbogen, John A.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhou, Dong</au><au>Chu, Wenhua</au><au>Voller, Thomas</au><au>Katzenellenbogen, John A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-mediated nucleophilic radiobromination of aryl boron precursors: Convenient preparation of a radiobrominated PARP-1 inhibitor</atitle><jtitle>Tetrahedron letters</jtitle><addtitle>Tetrahedron Lett</addtitle><date>2018-05-16</date><risdate>2018</risdate><volume>59</volume><issue>20</issue><spage>1963</spage><epage>1967</epage><pages>1963-1967</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>[Display omitted]
•Copper-mediated nucleophilic radiobromination of aryl boron precursors.•Broad scope of aryl boron precursors.•Efficient and robust radiolabeling reactions.•High yield and feasible purification.•Used for the facile synthesis of a radiobrominated PARP-1 inhibitor.
The copper-mediated nucleophilic radiobromination of aryl boron precursors with a radiobromide ion is a novel radiolabeling method that is efficient and robust. High radiochemical conversion (RCC) was observed using a variety of solvents, temperatures and catalysts. The reaction is also clean and is feasible for purification to obtain high chemical and radiochemical purity. This method provides a very useful route for the preparation of radiobrominated pharmaceuticals, including a radiobromine labeled PARP-1 inhibitor, and it is a valuable addition to the family of copper-mediated radiolabeling processes.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>30349147</pmid><doi>10.1016/j.tetlet.2018.04.024</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0040-4039 |
| ispartof | Tetrahedron letters, 2018-05, Vol.59 (20), p.1963-1967 |
| issn | 0040-4039 1873-3581 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_6195330 |
| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Auger electron radiation Boron reagents Bromine-76 Bromine-77 Labeling method Nucleophilic radiobromination PET imaging |
| title | Copper-mediated nucleophilic radiobromination of aryl boron precursors: Convenient preparation of a radiobrominated PARP-1 inhibitor |
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